US5889062A - Compositions and methods for the treatment of aging skin - Google Patents

Compositions and methods for the treatment of aging skin Download PDF

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Publication number
US5889062A
US5889062A US08/718,592 US71859296A US5889062A US 5889062 A US5889062 A US 5889062A US 71859296 A US71859296 A US 71859296A US 5889062 A US5889062 A US 5889062A
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Prior art keywords
skin
formulations
weight
plastoquinones
ubiquinones
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US08/718,592
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English (en)
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Udo Hoppe
Gerhard Sauermann
Volker Schreiner
Klaus-Michael Steiger
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Beiersdorf AG
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Beiersdorf AG
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Assigned to BEIERSDORF AKTIENGESELLSCHAFT reassignment BEIERSDORF AKTIENGESELLSCHAFT ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: STEIGER, KLAUS-MICHAEL, SCHREINER, VOLKER, SAUERMANN, GERHARD, HOPPE, UDO
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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35—Ketones, e.g. benzophenone
    • A61K8/355—Quinones
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/67—Vitamins
    • A61K8/671—Vitamin A; Derivatives thereof, e.g. ester of vitamin A acid, ester of retinol, retinol, retinal
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/08—Anti-ageing preparations

Definitions

  • the present invention relates to active compounds and formulations for care of aged skin and for prophylaxis and treatment of chronological aging of the skin which may additionally be intensified or accelerated by exogenous factors.
  • Exogenous factors such as UV light and chemical noxae, may have a cumulative action and, for example, accelerate or supplement the endogenous aging processes.
  • Exogenous factors such as UV light and chemical noxae, may have a cumulative action and, for example, accelerate or supplement the endogenous aging processes.
  • the epidermis and dermis for example, the following structural damage and dysfunctions in the skin, which go beyond the extent and quality of damage during chronological aging, occur in particular due to exogenous factors:
  • the present invention particularly relates to products for care of skin aged in a natural manner, and for treatment of the secondary damage of aging caused by light, in particular the phenomena listed under a) to g).
  • Products for the care of aged skin are known per se. They comprise, for example, retinoids (vitamin A acid and/or derivatives thereof) or vitamin A and/or derivatives thereof.
  • retinoids vitamin A acid and/or derivatives thereof
  • Vitamin A and/or derivatives thereof the extent of their action on structural damage is limited.
  • the use of products comprising vitamin A acid moreover often causes severe erythematous skin irritations. Retinoids can therefore be employed only in low concentrations.
  • Cosmetic formulations with coenzyme Q-10 which are suitable for treatment of skin diseases, for prophylaxis of dystrophic and dysmetabolic states of the skin and for use on chemical and physical respiratory damage or in cases of delayed respiration associated with age and wear are furthermore known from DE-A-33 09 850.
  • Japanese Laid-Open Specification 58,180,410 describes the suitability of coenzyme Q-10 for cosmetics. It is said to activate skin cell metabolism and suppress oxidation. As a result, coenzyme Q-10 has an important function in the prevention of skin damage due to UV radiation and the prevention of aging of the skin. Roughness of the skin of 20- to 40-year olds is improved by giving the skin moisture.
  • the object of the present invention was thus to discover ways of avoiding the disadvantages of the prior art.
  • the action of eliminating the damage associated with endogenous, chronological and exogenous aging of the skin and prophylaxis should be permanent, lasting and without the risk of side effects.
  • the invention relates to topical formulations having a content of one compound or several compounds from the group consisting of ubiquinones and derivatives thereof in combination with a content of one compound or several compounds from the group consisting of plastoquinones and derivatives thereof, or formulations having a content of one compound or more compounds from the group consisting of plastoquinones and derivatives thereof (as only one group of active compounds).
  • topical formulations according to the invention can be cosmetic or dermatological formulations. They are preferably used, as are also the active compounds, for prophylaxis and/or treatment of aging of the skin of chronological and/or exogenous origin.
  • the invention also relates to the use of one compound or several compounds from the group consisting of ubiquinones and derivatives thereof in combination with one compound or several compounds from the group consisting of plastoquinones and derivatives thereof, or the use of one compound or several compounds from the group consisting of plastoquinones and derivatives thereof, in each case for prophylaxis and/or treatment of aging of the skin of chronological and/or exogenous origin.
  • Ubiquinones and "plastoguinones” here also mean “ubiquinones and derivatives thereof” and “plastoquinones and derivatives thereof”.
  • ubiquinones and derivatives thereof and/or plastoquinones and derivatives thereof not only protect the skin from damage due to chronological aging of the skin, but in particular aging caused by light, but also bring about the repair of damage, which significantly remedies disadvantages of the prior art.
  • This action of this group of substances on structural changes of aged skin is particularly advantageous.
  • Ubiquinones are known from the literature (for example "Rompp Chemie Lexikon” Rompp's Chemical Dictionary!, Georg Thieme Verlag, Stuttgart, N.Y., 9th Edition, pages 4784-4785 or "The Merck Index", 11th Edition, Merck & Co., Inc. Rahway, N.Y., USA, Abstract 9751 (1989)). They are also called mitoquinones or coenzymes Q. The number of isoprene units in the side chain is stated with n in the designation coenzymes Q-n, wherein n is an integer.
  • the invention thus also relates to the quinone parent substance of ubiquinone without isoprene substituents.
  • Ubiquinones according to the invention or derivatives thereof are also, for example, alkyl-ubiquinones, in particular 6-alkyl-ubiquinones, with preferably C 1 -C 12 -alkyl radicals.
  • Preferred compounds are decyl-ubiquinone, in particular 6-decyl-ubiquinone, or 2,3-dimethoxy-5-methyl-6-decyl-1,4-benzoquinone.
  • the plastoquinones are likewise known from the literature (for example "Rompp Chemie Lexikon” Ropp'Chemical Dictionary!, Georg Thieme Verlag, Stuttgart, N.Y., 9th Edition, page 3477). They are closely related to the ubiquinones in structure and are also counted among the isoprenoid quinones, since they carry a side chain of isoprene units on the quinone ring. Preferred plastoquinones are those having 0-12, particularly preferably 1-10, and in particular 6 to 10, isoprene units in the side chain. The invention thus also relates to the quinone parent substance of plastoquinone without isoprene substituents.
  • Plastoquinones according to the invention or derivatives thereof are, for example, also alkyl-plastoquinones with preferably C 1 -C 12 -alkyl radicals.
  • Preferred compounds are decyl-plastoquinones, in particular 5- or 6-decyl-plastoquinone, or 2,3-dimethyl-5-decyl-1,4-benzoquinone.
  • ubiquinones During biological mitochondrial oxidation, ubiquinones function as electron transfer agents and thus play an important role in energy metabolism of animal cells. Ubiquinones have been used for a long time in cosmetic formulations as antioxidants for protection of oxidation-sensitive substances.
  • Plastoquinones are analogous compounds from the plant kingdom which play a role in photosynthesis in the chloroplasts of plant cells. They differ from ubiquinones in three substituents on the quinone ring, where the two methoxy groups in the ubiquinones are replaced by methyl groups and one methyl group is replaced by a hydrogen atom. However, the isoprene units bonded in the form of a chain have the same structure (cf., for example, Pfister and Arntzen, Z. fur Naturforschung C34; 996 et seq., 1979).
  • Coenzyme Q-10 coenzyme Q-9, coenzyme Q-8, coenzyme Q-7, coenzyme Q-6,
  • plastoquinone with 10 isoprene units also called PQ-10, corresponding to the IUB abbreviation PQ for plastoquinones, in the formula PQ-n, n is intended to indicate the number of isoprene units (0 to 12)), PQ-9, PQ-8, PQ-7 and PQ-6.
  • the active compound combinations or active compounds according to the invention can be present in the topical formulations in amounts of 0.001 to 99% by weight, for example also in amounts of 0.001 to 50% by weight, in each case based on the total weight of the formulations.
  • the active compound combinations or active compounds according to the invention can preferably be present in the topical formulations in amounts of 0.01 to 10% by weight, in particular in amounts of 0.1 to 1% by weight, in each case based on the total weight of the formulations.
  • the weight ratios of the two components in the ubiquinone/plastoquinone combinations can vary within wide limits, for example in the ratio from 1:100 to 100:1, preferably in the ratio from 1:10 to 10:1.
  • the components can also be present, for example, in the weight ratio from 1:2 to 2:1 or 1:1.
  • the skin care products or dermatological agents especially preferably comprise 0.2 to 0.4% by weight, in particular 0.3% by weight, of coenzyme Q-10 in combination with one or more plastoquinones or derivatives thereof.
  • Topical formulations or compositions according to the invention with the combinations and active compounds according to the invention are all the customary use forms, for example creams (W/O, O/W or W/O/W), gels, lotions and milks.
  • the topical formulations according to the invention can be formulated as liquid, pasty or solid formulations, for example as aqueous or alcoholic solutions, aqueous suspensions, emulsions, ointments, creams, oils, powders or sticks.
  • the active compounds can be incorporated into pharmaceutical and cosmetic bases for topical applications which comprise, as further components, for example, oil components, fat and waxes, emulsifiers, anionic, cationic, ampholytic, zwitterionic and/or nonionic surfactants, lower mono- and polyhydric alcohols, water, preservatives, buffer substances, thickeners, fragrances, dyestuffs and opacifying agents.
  • the active compounds according to the invention can also advantageously be used in transdermal therapeutic systems, in particular cubic systems.
  • antioxidants for example alpha-tocopherol, vitamin E and C, imidazoles, alpha-hydroxycarboxylic acids (for example malic acid, glycolic acid, gluconic acid, salicylic acid and derivatives thereof) and/or iron-complexing agents (for example EDTA or alpha-hydroxy-fatty acids) and/or known UV light protection filters, in amounts of, for example, 0.1 to 10 per cent by weight, in order to ensure the stability of the oxidation-sensitive ubiquinones or plastoquinones.
  • antioxidants for example alpha-tocopherol, vitamin E and C, imidazoles, alpha-hydroxycarboxylic acids (for example malic acid, glycolic acid, gluconic acid, salicylic acid and derivatives thereof) and/or iron-complexing agents (for example EDTA or alpha-hydroxy-fatty acids) and/or known UV light protection filters, in amounts of, for example, 0.1 to 10 per cent by weight, in order to ensure the stability of the oxidation-sensitive ubiquino
  • cell energy transfer agents such as kreatin, guanine, guanosine, adenine, adenosine, nicotine, nicotinamide or riboflavin
  • coenzymes for example pantothenic acid, panthenol, liponic acid or niacin
  • auxiliary factors for example L-carnitine, or uridine
  • substrates for example hexoses, pentoses or fatty acids
  • intermediate metabolism products for example citric acid or pyruvate
  • Formulations according to the invention can advantageously moreover comprise substances which absorb UV radiation in the UVA and/or UVB range, the total amount of filter substances being, for example, 0.1% by weight to 30% by weight, preferably 0.5 to 10% by weight, in particular 1.0 to 6.0% by weight, based on the total weight of the formulations, in order to provide cosmetic formulations which protect the skin against the entire range of ultraviolet radiation. They can also be used as sunscreen formulations for the skin.
  • the UV absorbers act as antioxidants with respect to the active compounds.
  • the emulsions according to the invention comprise UVB filter substances, these can be oil-soluble or water-soluble.
  • Oil-soluble UVB filters which are advantageous according to the invention are, for example: 3-benzylidenecamphor derivatives, preferably 3- (4-methylbenzylidene)camphor and 3-benzylidenecamphor.
  • Advantageous water-soluble UVB filters are, for example:
  • salts of 2-phenylbenzimidazole-5-sulphonic acid such as its sodium, potassium or its triethanolammonium salt, and the sulphonic acid itself.
  • UVA filters which have usually been contained to date in cosmetic formulations.
  • These substances are preferably derivatives of dibenzoylmethane, in particular 1-(4'-tert-butylphenyl)-3-(4'-methoxyphenyl)propane-1,3-dione and 1-phenyl-3-(4'-isopropylphenyl)propane-1,3-dione.
  • the invention also relates to these combinations or formulations which comprise these combinations. The amounts employed for the UVB combination can be used.
  • the invention thus also relates to the combinations of the active compounds according to the invention, in particular in the topical formulations, with anti-oxidants, substances of aerobic cell energy metabolism and/or UV absorbers, with which, for example, the stability and the action of the formulation can be improved.
  • Protective formulation forms can furthermore be used, the substances according to the invention being enclosed (encapsulated), for example, in liposomes, micelles, nanospheres and the like of, for example, hydrogenated amphiphiles, such as, for example, ceramides, fatty acids, sphingomyelin and phosphoglycerides, or in cyclodextrans. Further protection can be achieved by the use of inert gas (for example N 2 or CO 2 ) during formulation and the use of gas-tight packaging forms.
  • inert gas for example N 2 or CO 2
  • auxiliaries and additives can be water-binding substances, thickeners, fillers, perfume, dye-stuffs, emulsifiers, active compounds such as vitamins, preservatives, water and/or salts.
  • the temperature should not be above 40° C. Otherwise, the usual rules, which are known to the expert, are to be observed.
  • the substance groups according to the invention can thus be incorporated into all cosmetic bases. In principle, however, W/O, O/W and W/O/W emulsions are preferred. Combinations according to the invention can be employed particularly advantageously in care products such as, for example, O/W creams, W/O creams, O/W lotions, W/O lotions and the like.
  • aqueous phase heated to 75° C.
  • fat phase heated to 75° C.
  • components are stirred and homogenized until a uniformly white cream has formed.
  • 0.03 part of plastoquinone having 9 isoprene groups (PQ-9) are dissolved in 8.5 parts of paraffin oil, the solution is added to the cream, which has cooled to about 40° C., and the components are stirred until a uniform pale yellow cream has formed.
  • Example I has the following final composition:
  • the aqueous phase heated to 75° C.
  • the fat phase heated to 75° C.
  • the components are stirred and homogenized until a uniformly white cream has formed.
  • 0.36 part of coenzyme Q-10 and 0.04 part of plastoquinone with 9 isoprene groups, PQ-9, are dissolved in 2 parts of paraffin oil, the solution is added to the cream, which has cooled to about 40° C., and the components are stirred until a uniform pale yellow cream has formed.
  • Example II has the following final composition:
  • the aqueous phase heated to 75° C.
  • the fat phase heated to 75° C.
  • the components are stirred and homogenized until a uniformly white cream has formed.
  • 0.54 part of coenzyme Q-10 and 0.35 part of coenzyme Q-6 and 0.01 part by weight of plastoquinone PQ-9 are dissolved in 2 parts of paraffin oil, the solution is added to the cream, which has cooled to about 40° C., and the components are stirred until a uniform pale yellow cream has formed.
  • Example III has the following final composition:
  • the aqueous phase heated to 75° C.
  • the fat phase heated to 75° C., and the components are stirred and homogenized until a uniformly white lotion has formed.
  • 0.2 part of coenzyme Q-10 and 0.2 part of plastoquinone PQ-9 are dissolved in 4 parts of paraffin oil, the solution is added to the lotion, which has cooled to about 40° C., and the components are stirred until a uniform pale yellow lotion has formed.
  • Example IV has the following final composition:
  • the aqueous phase heated to 75° C.
  • the fat phase heated to 75° C.
  • the components are stirred and homogenized until a uniformly white cream has formed.
  • 0.04 part of coenzyme Q-10 and 0.36 part of plastoquinone PQ-9 are dissolved in 5 parts of paraffin oil, the solution is added to the cream, which has cooled to about 40° C., and the components are stirred until a uniform pale yellow cream has formed.
  • Example V has the following final composition:
  • the components are stirred at 25° C. until a uniform, clear mixture has formed.
  • the aqueous phase heated to 75° C.
  • the fat phase heated to 75° C.
  • the components are stirred and homogenized until a uniformly white cream has formed.
  • 0.27 part of coenzyme Q-10 and 0.03 part by weight of plastoquinone PQ-6 are dissolved in 8.5 parts of paraffin oil, the solution is added to the cream, which has cooled to about 40° C., and the components are stirred until a uniform pale yellow cream has formed.
  • Example VIII has the following final composition:

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
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  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Dermatology (AREA)
  • Emergency Medicine (AREA)
  • Gerontology & Geriatric Medicine (AREA)
  • Cosmetics (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicinal Preparation (AREA)
  • Bakery Products And Manufacturing Methods Therefor (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
US08/718,592 1994-03-25 1995-03-24 Compositions and methods for the treatment of aging skin Expired - Fee Related US5889062A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4410238.0 1994-03-25
DE4410238A DE4410238A1 (de) 1994-03-25 1994-03-25 Hautpflegemittel
PCT/EP1995/001117 WO1995026181A1 (de) 1994-03-25 1995-03-24 Gegen hautalterung wirksame stoffe oder wirkstoffkombinationen und zubereitungen

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US08/718,592 Expired - Fee Related US5889062A (en) 1994-03-25 1995-03-24 Compositions and methods for the treatment of aging skin
US08/718,591 Expired - Lifetime US5912272A (en) 1994-03-25 1995-03-24 Active substances and compositions for the therapy of senile xerosis

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US08/718,591 Expired - Lifetime US5912272A (en) 1994-03-25 1995-03-24 Active substances and compositions for the therapy of senile xerosis

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US (2) US5889062A (de)
EP (3) EP0751762B1 (de)
JP (3) JPH09510724A (de)
AT (3) ATE197897T1 (de)
DE (4) DE4410238A1 (de)
ES (3) ES2154336T3 (de)
WO (3) WO1995026181A1 (de)

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DE19944137A1 (de) * 1999-09-15 2001-03-22 Beiersdorf Ag O/W-Emulsionen mit einem Gehalt an einem oder mehreren Biochinonen und einem erhöhten Gehalt an Glycerin
WO2001074361A1 (en) * 2000-04-04 2001-10-11 Sigma-Tau Healthscience S.P.A. Dietary supplement energy-providing to skeletal muscles and protecting the cardiovascular tract
WO2002009652A3 (de) * 2000-07-28 2002-07-25 Beiersdorf Ag Carnitin enthaltende kosmetische oder dermatologische wirkstoffkombinationen und deren verwendung
WO2002078651A1 (en) * 2001-04-02 2002-10-10 Alberto-Culver Company Cosmetic composition with improved skin moisturizing properties
US6503523B2 (en) 1998-05-07 2003-01-07 Gs Development A.B. Skin care agents containing combinations of active agents consisting of vitamin a derivatives and UBI- or plastoquinones
US20030180277A1 (en) * 2000-07-28 2003-09-25 Udo Hoppe Use of bioquinones for producing cosmetic or dermatological preparations for treating the hair and scalp
US20040197282A1 (en) * 1999-07-09 2004-10-07 Birgit Neudecker Method and preparation containing idebenone for protecting human skin
US20050036976A1 (en) * 2003-08-12 2005-02-17 Joel Rubin Topical skin care composition
US20050070611A1 (en) * 2003-09-29 2005-03-31 Michael Fantuzzi Solubilized CoQ-10
US20050069582A1 (en) * 2003-09-29 2005-03-31 Michael Fantuzzi Solubilized CoQ-10
US20050079164A1 (en) * 2003-09-29 2005-04-14 Michael Fantuzzi Solubilized CoQ-10 and carnitine
US6906106B2 (en) * 2001-03-23 2005-06-14 L'oreal Compositions for the skin comprising fibers and ubiquinones and methods of using the same
US20050175559A1 (en) * 2004-02-10 2005-08-11 Pcr Technology Holdings, Lc Method and preparation for reducing skin hyperpigmentation
US20050186158A1 (en) * 1999-06-25 2005-08-25 Avicena Group, Inc. Use of creatine or creatine compounds for skin preservation
US20050197407A1 (en) * 2004-02-13 2005-09-08 Pcr Technology Holdings, Lc Method and preparation for reducing irritation and/or inflammatory reaction in human skin
US20060002885A1 (en) * 2004-07-02 2006-01-05 Beiersdorf Ag Use of combinations of active ingredients of one or more bioquinones and one or more isoflavones for improving the contours of the skin
US20060057188A1 (en) * 2000-04-04 2006-03-16 Franco Gaetani Dietary supplement energy-providing to skeletal muscles
US20060251690A1 (en) * 2005-04-01 2006-11-09 Zymes, Llc Skin enrichment using CoQ10 as the delivery system
US20060275358A1 (en) * 2005-06-01 2006-12-07 Cardinal Health Australia 401 Pty. Ltd. Self-microemulsifying dosage forms of low solubility active ingredients such as co-enzyme Q10
US20070270732A1 (en) * 2003-06-23 2007-11-22 Transpharma Medical Ltd. Transdermal Delivery System for Cosmetic Agents
US20080089877A1 (en) * 2003-08-14 2008-04-17 Udell Ronald G Super Absorption Coenzyme Q10
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US20080299100A1 (en) * 2004-01-22 2008-12-04 University Of Miami Topical Co-Enzyme Q10 Formulations and Methods of Use
US20090105196A1 (en) * 2007-06-22 2009-04-23 Belinda Tsao Nivaggioli Use of creatine compounds to treat dermatitis
US20100010100A1 (en) * 2008-07-09 2010-01-14 Hinman Andrew W Dermatological compositions with anti-aging and skin even-toning properties
US20100029784A1 (en) * 2008-07-30 2010-02-04 Hinman Andrew W Naphthoquinone compositions with anti-aging, anti-inflammatory and skin even-toning properties
US20110027247A1 (en) * 2009-05-11 2011-02-03 Niven Rajin Narain Methods for treatment of oncological disorders using an epimetabolic shifter (coenzyme q10)
US20110229554A1 (en) * 2010-03-12 2011-09-22 Niven Rajin Narain INTRAVENOUS FORMULATIONS OF COENZYME Q10 (CoQ10) AND METHODS OF USE THEREOF
US8454945B2 (en) 2007-03-22 2013-06-04 Berg Pharma Llc Topical formulations having enhanced bioavailability
US8506995B2 (en) 1999-03-29 2013-08-13 Soft Gel Technologies, Inc. Coenzyme Q10 formulation and process methodology for soft gel capsules manufacturing
US9901542B2 (en) 2013-09-04 2018-02-27 Berg Llc Methods of treatment of cancer by continuous infusion of coenzyme Q10
US10376477B2 (en) 2011-04-04 2019-08-13 Berg Llc Method of treating or preventing tumors of the central nervous system
US10668028B2 (en) 2008-04-11 2020-06-02 Berg Llc Methods and use of inducing apoptosis in cancer cells
US10933032B2 (en) 2013-04-08 2021-03-02 Berg Llc Methods for the treatment of cancer using coenzyme Q10 combination therapies
US10973763B2 (en) 2011-06-17 2021-04-13 Berg Llc Inhalable pharmaceutical compositions
US12303471B2 (en) 2015-11-16 2025-05-20 Bpgbio, Inc. Methods of treatment of temozolomide-resistant glioma using coenzyme Q10

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WO1998035658A2 (de) * 1997-02-12 1998-08-20 Mse Pharmazeutika Gmbh Verwendung von 2,3-dimethoxy-5-methyl-6-decaprenyl-1,4-benzochinon
US5855893A (en) 1997-02-14 1999-01-05 Elizabeth Arden Co., Division Of Conopco, Inc. Trichodesma lanicum seed extract as an anti-irritant in compositions containing hydroxy acids or retinoids
DE19820392A1 (de) * 1998-05-07 1999-11-11 Beiersdorf Ag Wirkstoffkombinationen enthaltende Hautpflegemittel
DE19839402A1 (de) * 1998-08-29 2000-03-02 Beiersdorf Ag Retinoide enthaltende Hautpflegemittel
DE19918750A1 (de) * 1999-04-24 2000-10-26 Beiersdorf Ag Wirkstoffe, kosmetische und dermatologische Zubereitungen für die Verbesserung der Barrierefunktion
IT1306141B1 (it) * 1999-05-17 2001-05-30 Giampiero Valletta Composizione per il trattamento del prurito uremico e di forme diprurito non riconducibili a lesioni organiche.
DE19926167B4 (de) * 1999-06-09 2012-08-30 Henkel Ag & Co. Kgaa Aerosol-Stylingmittel auf Wasserbasis mit Biochinonen
DE19926156A1 (de) * 1999-06-09 2000-12-14 Beiersdorf Ag Haarkosmetische Zubereitungen insbesondere solche zur Verbesserung der Kämmbarkeit der Haare auf der Grundlage von Ubichinonen
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ATE197897T1 (de) 2000-12-15
WO1995026181A1 (de) 1995-10-05
US5912272A (en) 1999-06-15
EP0751762A1 (de) 1997-01-08
ES2242958T3 (es) 2005-11-16
JPH09510725A (ja) 1997-10-28
EP0751761A1 (de) 1997-01-08
EP0751763B1 (de) 2001-10-24
ES2154336T3 (es) 2001-04-01
DE59511002D1 (de) 2005-07-07
JPH09510724A (ja) 1997-10-28
EP0751762B1 (de) 2000-12-06
ATE207342T1 (de) 2001-11-15
DE59508891D1 (de) 2001-01-11
ATE296612T1 (de) 2005-06-15
DE4410238A1 (de) 1995-09-28
WO1995026180A1 (de) 1995-10-05
WO1995026182A1 (de) 1995-10-05
DE59509751D1 (de) 2001-11-29
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JPH09510723A (ja) 1997-10-28
EP0751763A1 (de) 1997-01-08

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